In 1998, after an extensive interview process, Jon Wimbish, now the Head of the Middle School, was hired as a teacher in the middle school English Department. During the process, he said he met every member of the English Department except for a second year English teacher — Amanda Angle. Despite her short tenure at the school, Angle was assigned to be Wimbish’s teacher mentor, helping him navigate his first year at the school .
Some speculate that former Middle School English Department Chair Ellen Erlich strategically placed the two young professionals together as part of a matchmaking scheme, Wimbish said.
Over the summer, Angle reached out to Wimbish to introduce herself and suggested they get coffee or go for a hike for their first mentor-mentee meeting. Angle said Wimbish later told her that her outdoorsy suggestion made an impression on him.
“He was like, ‘Go for a hike?’ Who suggests that?’” Angle said. “So he thought I was a little odd that way, but I grew up in New York and was loving that California outdoor stuff.”
After their first meeting, Wimbish and Angle said they became fast friends. Wimbish said they started seriously dating around four years into their relationship, and, over time, students began to catch on to their chemistry .
“We had students [who] become interested in teachers’ lives, [and] we had students who would kind of tease us from time to time, like, ‘Oh, I saw you having lunch with Ms. Angle,’” Wimbish said. “One [student] in particular, who we both taught, was like, ‘You guys should try to figure this out.’”
Wimbish proposed to Angle on a July night in Vermont in 2003, and they got married <q data-camayak-comment=”” class=” collapsed”></q> in Sun Valley a year later. The couple now have two children — Franklin Wimbish ’25 and Lila Wimbish ’26.
Interoffice relationships, like this one, are not uncommon — over half of working Americans have caught feelings for a coworker, and over a quarter have acted on these feelings to have a non-platonic relationship, according to the Society for Human Resource Management. In some working environments, there are regulations as to who can date whom, but at the school, there are no strict rules for employee relationships, Director of Human Resources Clifford Hahn said.
“We recognize that this is a really amazing place and that we have a really great community,” Hahn said. “So, it’s not surprising that people might meet other great people here and decide that they like one another. We don’t have a policy against relationships for adult employees. We do expect that those individuals would disclose their relationship. The folks that work here are professionals, and we expect them to act professionally. We would expect that that relationship wouldn’t create any issues then for them or students or anyone else.”
Wimbish worked as an Upper School Dean before taking on the administrative role of Head of Middle School, which Wimbish said changed his professional responsibilities.
“My coming back to the middle school was a step into administration , but it also meant that whatever professional distance we might have had was coming to an end,” Wimbish said. “[This was] complicated by the fact that I’m technically her supervisor. The school and I are very clear about certain supervisory roles that I do not [have] with my own wife .”
Teacher relationships, as a subset of workplace romances, are relatively common at the school, as well as in the broader educational community.Marriages between elementary and middle school teachers are the most common marriages between two people of the same profession, according to Bloomberg.
Upper School Science Teacher Ryan Ellingson is married to Middle School Science Teacher Daniella Ellingson. He said teachers often work long hours, and their professional duties do not stop when they leave the office, so having a partner who understands their commitments is beneficial.
“[My spouse’s profession] is helpful because we understand each other’s situation,” Ellingson said. “I’ve heard other teachers talk about their significant other being frustrated about how often they have to do school things because in other professions, they don’t understand what teaching is. There [are] a lot of professions where you go to work, and then when you go home, work stays at work. Teaching is not one of those [professions].”
Likewise, Angle said it is helpful to have a mutual understanding of each others’ work lives.
“Overall, it’s just someone who gets it,” Angle said. “We don’t have to explain. Usually, a spouse has to give the whole backstory and what’s going on at work.”
Although there are benefits to marrying within the profession, workplace romances can offer their own challenges. Working in the same department or even merely feet away from one another can sometimes make a work-life balance challenging to achieve, according to Forbes.
Angle said it can be difficult at times to refrain from talking about work, especially because her entire family is involved at the school.
“I have to say the bad part is we have to really work at times to not always be talking about things that are Harvard-Westlake-related because it’s consumed both of our lives so much and [as well as having consumed] our children’s lives,” Angle said. “You have to have a little bit of another life as well.”
Upper School Math Teacher Amy Stout is in her first year of teaching at the school, where her desk in the math department is close to where her husband, Upper School Math Teacher Andy Stout, works. She said she enjoys how convenient their proximity at work is.
“It’s fun to be able to see him interact with his students,” Stout said. “It’s always been kind of abstract in terms of what he’s like at work, so [now] I get to see another side of him. That’s always nice. If something comes up at home, I can easily kind of address it faster than if I have to call him at work. It actually reminds me of grad school when we were both there, and I would see him all the time there. It’s kind of like, we’re just doing our math, and he’s there doing his math, and I’m doing my own separate math.”
Upper School English Teacher Jocelyn Medawar said she and her husband, Upper School English Teacher Jeremy Michaelson, enjoy working with one another because their jobs have been a fundamental part of their relationship.
“I think there are some couples that thrive because they work apart,” Medawar said. “Their days are separate, they have their own thing, and then they come together at the end of the day. Because we were friends and colleagues first, I think we really get a lot of good energy from doing the same job.”
Similarly to Wimbish and Angle, Michaelson and Medawar met when Michaelson started at the school 27 years ago. The couple were friends for a long time, but they became more than that a few years before their marriage in 2020, Michaelson said.
“We had been friends for so long,” Michaleson said. “We kind of looked at each other. And we were like, ‘Wait, I think we can make this work.’ We just came to that naturally and then decided to give it a shot. It wasn’t like one of us was scared to ask the other out. It didn’t really didn’t work that way, because of the nature of our longstanding friendship.”
Michaelson and Medawar were married over Zoom by the Santa Barbara Courthouse, with Michaelson’s stepmother, his daughter and her boyfriend in attendance, Michaelson said.
“[The wedding] was something that we had to throw together because of the exigent circumstances of the pandemic, but we both agreed that making it happen in those circumstances made it really romantic,” Michaelson said. “So even though I cringed to look at my wedding pictures, because this is pre-any haircuts, I’m delighted that we made the effort to go through with it and did it despite the fact that there were a lot of obstacles.”
As students and alumni of the school heard that the couple had made it official, Medawar and Michaelson began receiving well wishes from past and present students, Medawar said.
“The outpouring of student support and love and care was delightful,” Medawar said. “The notes and beautiful sentiments that were expressed [by alumni] were really nice. People just seemed happy for us. [It was] So sweet.”
Not only do their students care deeply about them, but Michaelson and Medawar alsocare deeply about their students. Medawar said that, while she and Michaelson do talk about students at home, they do so in a professional manner to best serve the student.
“We do have some students in common,” Medawar said. “It would be unnatural not to talk about the students at home in the same way that [students] talk about teachers. But honestly, we don’t talk about students as much as one might think. But in the same way that you might go to any colleague, we’ll ask each other because it’s just part of doing a good job.”
Another part of doing a good job is being passionate about one’s work, according to Jobacle.com.
Medawar said her and Michaelson’s love for reading means they do not always need boundaries between the professional and personal, but they do like taking breaks from work.
“We love talking about books, so that means we love talking about our jobs, but there is still that work-life balance,” Medawar said. “And there are those times where we need to not be thinking about school right now, and we’ll go out and take a walk or we’ll watch a movie or go to a museum or just have lives that have nothing to do with school.”
While Michaelson and Medawar sometimes have to take a break from work at home, they never leave their love for reading at the door, Medawar said.
“I guess one would probably walk into our house and guess that we were English teachers,” Medawar said. “There are books in bins. There are books on shelves. There are shelves with books three, like three stacks. Even when we purge a whole bunch of books, more just grow. Books everywhere.”
Michaelson and Medawar said they also enjoy watching and reading together.
“We had this big puzzle that we were working on and we decided to rewatch ‘Pride and Prejudice’, the six hour BBC version,” Michaelson said. “We’re sitting there doing the puzzle and reciting the lines as they’re happening. And then Ms. Medawar just starts cracking up. And I’m like, ‘What’s up?’ She’s like, ‘This is exactly what our students think we do at night.’”
Both Michaelson and Medawar separately described one another as being each other’s “person.” Michaelson said that he loves Medawar, so, when asked what his favorite time with her was, he said he could not choose just one because he enjoys spending time with her so much.
“When it’s your person, it doesn’t really matter what you’re doing,” Michaelson said.”We’ve done a lot of fun things. We shared a lot of great memories, but to pin it down to just one is kind of impossible.”
